3-Methoxyluteolin

Base Information

• Chemical Name: 3-Methoxyluteolin
• CAS No.: 1486-70-0
• Molecular Formula: C16H12 O7
• Molecular Weight: 316.267
• Hs Code.: 2914509090
• European Community (EC) Number: 664-271-2
• UNII: 7J92C373RH
• ChEMBL ID: CHEMBL163316
• DSSTox Substance ID: DTXSID20164032
• Metabolomics Workbench ID: 25812
• Nikkaji Number: J876A
• NSC Number: 154016
• Wikidata: Q23068616
• Mol file: 1486-70-0.mol

Synonyms:3,4',5,7-tetrahydroxy-3'-methoxy-flavone;3,4',5,7-tetrahydroxy-3'-methoxyflavone;3-methyl-quercetin;3-methylquercetin;3-O-methylquercetin;iso-rhamnetin;isorhamnetin;isorhamnetine

Chemical Property of 3-Methoxyluteolin

Chemical Property:

• Melting Point: 275 °C
• Boiling Point: 643°Cat760mmHg
• PKA: 6.31±0.40(Predicted)
• Flash Point: 244.7°C
• PSA: 120.36000
• Density: 1.69g/cm³
• LogP: 2.29100
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 316.05830272
• Heavy Atom Count: 23
• Complexity: 503

Purity/Quality:

≥98% ^*data from raw suppliers

3-O-MethylQuercetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC(=C(C=C3)O)O
• Description: 3-O-Methylquercetin is a metabolite in flavone and flavonol biosynthesis. It is a naturally occurring compound present in various plants, and was shown to have potent anticancer-promoting, antioxidant, antiallergy, and antimicrobial activity, and showed strong anti-viral activity inhibition of tomato ringspot virus.3-O-Methylquercetin significantly inhibits cyclic adenosine monophosphate- (cAMP-) and cyclic guanosine monophosphate- (cGMP-) phosphodiesterase activity. It possess anti-inflammatory, bronchodilating properties and used in treatment of asthma. It suppresses the total inflammatory cells, tumor necrosis factor-α (TNF-α) and attenuates the production of interleukins.
• Uses: A metabolite of the flavanoid Quercetin (Q509500) with inhibitory activity on lipopolysaccharide-induced activation of macrophage U937 cells.

Technology Process of 3-Methoxyluteolin

There total 31 articles about 3-Methoxyluteolin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3',4'-bis(benzyloxy)-5,7-dihydroxy-3-methoxyflavone (1486-61-9) → 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on (1486-70-0)

Guidance literature:

With cyclohexene; palladium dihydroxide; In ethanol; for 0.5h; Heating;

DOI:10.1002/ardp.19973300909

Reference yield: 97.0%

2-(3,4-bis(benzyloxy)phenyl)-7-(benzyloxy)-5-hydroxy-3-methoxy-4H-chromen-4-one (1486-57-3) → 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on (1486-70-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 50 ℃;

Reference yield: 93.0%

7-(benzyloxy)-2-(4-(benzyloxy)-3-hydroxyphenyl)-5-hydroxy-3-methoxy-4H-chromen-4-one → 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on (1486-70-0)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; In ethanol; cyclohexene; for 1h; Inert atmosphere; Reflux;

DOI:10.1021/acs.jafc.0c04500

upstream raw materials:

2-methoxy-1-(2,4,6-trihydroxyphenyl)ethanone

3,4-bis-benzoyloxy-benzoic acid-anhydride

quercetol

3',4'-bis(benzyloxy)-5,7-dihydroxy-3-methoxyflavone

Downstream raw materials:

3,4'-O-dimethylquercetin

2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one

ayanin

3,3'-di-O-methylquercetin

Refernces

• 1、 Docampo-Palacios, Maite L.,Alvarez-Hernández, Anislay,Adiji, Olubu,Gamiotea-Turro, Daylin,Valerino-Diaz, Alexander B.,Viegas, Luís P.,Ndukwe, Ikenna E.,De Fátima, ?ngelo,Heiss, Christian,Azadi, Parastoo,Pasinetti, Giulio M.,Dixon, Richard A.. "Glucuronidation of Methylated Quercetin Derivatives: Chemical and Biochemical Approaches". . p. 14790 - 14807. Retrieved 2020/12/23.
• 2、 El-Meligy, Asmaa B.,Ishihara, Takehiro,Oyama, Kin-Ichi,El-Nahas, Ahmed M.,Yoshida, Kumi. "The first synthesis of 3-O-methylcyanidin and the effect of 3-O-substitution on stability under acidic conditions". . p. 946 - 959. Retrieved 2019/04/26.